Functionalized particles

ABSTRACT

Functionalized particles comprising a shell and a core and a payload that is embedded or entrapped, wherein the shell matrix is obtained by interfacial polymerisation of vinyltriethoxy silane and at least one other ethylenically unsaturated monomer copolymerizable with vinyltriethoxy silane, said functionalized particles being capable to chemically bind to a substrate, are suitable as controlled release systems for textile applications to impart durable softness and excellent water retention even after multiple laundries.

The present invention relates to functionalized particles or capsuleshaving a shell core configuration, wherein the polymeric shell comprisesa matrix obtained by interfacial polymerisation of certain ethylenicallyunsaturated monomers. The particles may be used as microcontainers toencapsulate different substances or payloads. The particles havefunctional groups which are capable to permanently bind to the surfaceof substrates, such as textiles. This invention relates further to thepreparation of the functionalized particles.

The technique of microencapsulation has achieved increasing importance,since this method enables substances of various states of aggregation tobe enclosed. Microcapsules have been used as carriers for variouspayloads, such as, for example, inks and dyestuffs, odor or flavorsubstances, pharmaceutically active formulations, chemical reagents andplant protection agents.

Encapsulation of active compounds can be advantageous in reducing theodor nuisance in the case of odor-intensive active compounds. A furtheradvantage of encapsulation is that it is thereby possible to achieverelease of the active compound in a controlled manner with respect totime and amount (depot action). As a result of this “slow release”effect, the active compound can remain active over a longer period andcan thereby be better utilized, the number of applications necessary canbe decreased and hence, finally, the total amount of active compound tobe applied can be reduced.

Numerous mechanical and chemical processes for manufacturing of thecapsules have already been described and used, for example, J. E.Vandegaer, “Microencapsulation”, Plenum-Press, New York-London; 1974.Preparation is suitably carried out by interfacial polymerization,wherein the monomers polymerise at the interface between a dispersedphase and a continuous phase to form a shell around the dispersed phase.

Recently, microcapsules containing active agents have been applied alsoin the textile industry. Microcapsules allow for example for fragrancesand perfumes or antimicrobial substances to be encapsulated. Such agentsare released and impart fragrance or an antimicrobial effect to thefinished textile material in order to reduce or prevent malodors due toperspiration. Furthermore, textiles have been finished withmicrocapsules containing phase change materials for thermoregulation. Intextile application it is desired that the effect imparted stayspermanent. Accordingly, the microcapsules have to permanently bind tothe textile and resist repeated washing cycles during usage of theapparel. Nanoparticles for the permanent treatment of textiles aredescribed, for example, in U.S. Pat. No. 6,607,994.

Fabric softeners improve different properties of textile such as softhand (supple, pliant, sleek and fluffy), smoothness, flexibility,drapability and pliability. Fabric softeners may be cationic, anionic ornonionic depending on the purposes of end uses. Generally, fabricsofteners are based on silicones, paraffins and polyethylene. Nonionicand cationic silicone softeners are commercially adopted for research orindustrial purposes, because it provides higher softness, special uniquehand, high lubricity, good sewability, elastic resilience, creaserecovery and abrasion resistance.

Different approaches were accomplished to impart softener durability onfabrics, such as the application of citric acid or polyurethane basedresin along with silicone softener. However, incorporation of excessiveresin led to hamper fabric softness so that resins were not commerciallyadopted for this purpose. Silane coupling agent were used with siliconesoftener to improve durability. However, this approach has not beenproven commercially viable, because of higher product costs.Microencapsulation of softeners was suggested as a further approach toimpart wash durability.

The present invention accordingly relates to functionalized particlescomprising a shell and a core and a payload that is embedded orentrapped, wherein the shell matrix is obtained by interfacialpolymerisation of vinyltriethoxy silane and at least one otherethylenically unsaturated monomer copolymerizable with vinyltriethoxysilane, said functionalized particles being capable to chemically bindto a substrate.

The term “payload” as used herein refers to any material, substance,compound, agent, active material, active substance, active compound oractive agent that is embedded or entrapped by the functionalizedparticle and that may be released from the cage of the payloadcontaining particle in a controlled and/or prolonged fashion.

As the payload there come into consideration, for example, vitamines,phase change materials, catalysts, enzymes, biocides, antimicrobials,insecticides, acaricides, fungicides, herbicides, pheromones,fragrances, flavorings, softeners, pharmaceutical active compounds,cosmetic actives, active compounds for antistatic finishing or flameretardant finishing, UV-stabilizers, dyestuffs, pigments or mixturesthereof.

The functionalized particles can be used, for example, to

-   -   release active compounds in a controlled manner,    -   increase the bioavailability of active compounds,    -   increase the durability of active compounds on textiles against        laundering,    -   encapsulate phase change materials for textile application, such        as semisynthetic glycerides.    -   stabilize active compounds, e.g. to light, temperature,        oxidation, hydrolysis, evaporation by complex formation,    -   solubilize active compounds,    -   decrease toxicity or irritation of active compounds by        encapsulation.

The polymeric shell matrix comprises functional groups that providereactive radicals on the surface of the particle, which bind to groupsattached to the substrate that are capable to chemically react withreactive radicals of the particle shell matrix to form covalent bondsbetween the particle and the substrate and permanently fix the particleto the substrate.

If the substrate is a textile fabric, the functional groups on thesurface of the particles are selected from those groups that arereactive and will bind chemically to the textile fabric, such as to thehydroxyl groups of the cellulose based fabrics or the amine, carboxylateand thiol groups of wool or silk and other proteinaceous animal fibers.The reactive groups, for example, may contain epoxide groups or epoxideprecursors, such as halohydrins. Epoxides can react with amines andhydroxyl groups. Also, methylolacrylamide may be copolymerized into theparticle matrix, or monomers that are modified with anhydride groups, oralkoxy silanes that carry an ethylenically unsaturated group.

Textile fiber reactive radicals are well known in the art of fiberreactive dyes and described, for example, in Venkataraman “The Chemistryof Synthetic Dyes” Band 6, Seiten 1-209, Academic Press, New York,London 1972. WO 2006/013165 which is incorporated herein by referencedescribes suitable textile fiber reactive group precursors which comeinto consideration for the preparation of monomers carrying fiberreactive groups by reaction of a monomer precursor with the fiberreactive group precursor.

In a certain embodiment of the present invention the at least one otherethylenically unsaturated monomer is a hydrophobic monomer.

As hydrophobic monomers there are mentioned, for example, styrene,α-methyl styrene, glycidyl methacrylate, vinyl trimethoxysilane, methylmethacrylate, ethyl methacrylate, n-propyl methacrylate, n-butylmethacrylate, 3-(trimethoxysilyl)propyl acrylate,3-(trimethoxysilyl)propyl methacrylate, N-(tert-butyl)acrylamide,N-(n-decyl)acrylamide, n-decyl methacrylate, N-dodecylmethacrylamide,2-ethylhexyl acrylate, n-hexadecyl methacrylate, n-myristyl acrylate,N-(n-octadecyl)acrylamide, n-octadecyltriethoxysilane,tert-octylacrylate, stearyl acrylate, stearyl methacrylate, vinyllaurate or vinyl stearate, preferably styrene, glycidyl methacrylate,methyl methacrylate, ethyl methacrylate, 3-(trimethoxysilyl)propylacrylate or 3-(trimethoxysilyl)propyl methacrylate.

In an interesting embodiment of the present invention the at least oneother ethylenically unsaturated hydrophobic monomer is styrene orglycidyl methacrylate.

In another interesting embodiment of the present invention the at leastone other ethylenically unsaturated hydrophobic monomer is styrene andglycidyl methacrylate.

In yet another interesting embodiment of the present invention the shellmatrix is obtained by interfacial polymerisation of vinyltriethoxysilane and at least one other ethylenically unsaturated monomercopolymerizable with vinyltriethoxy silane and at least one hydrophilicmonomer.

As hydrophilic monomers there are mentioned, for example, acrylamide,methacrylamide, N-methylmethacrylamide, N-methylolacrylamide, acrylicacid, methacrylic acid, N-vinyl pyrrolidone,N-acryloyltris(hydroxymethyl)-methylamine, bisacrylamidoacetic acid,glycerol monoacrylate, glycerol monomethacrylate, 4-hydroxybutylmethacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate,N-(2-hydroxypropyl)methacrylamide, N-methacryloyltris(hydroxymethyl)methylamine, polyethylene glycol monomethacrylate,2-sulfoethyl methacrylate or 1,1,1-trimethylolpropane monoallyl ether,preferably acrylic acid, methacrylic acid or N-vinyl-2-pyrrolidone.

In a special embodiment of the present invention the payload is a fabricsoftener, especially a silicone softener. Depending on the morphologysilicone softeners might be hydrophilic or hydrophobic. Hydrophilicsilicone softeners are used mostly in terry towel. However, thesesilicone softeners have very limited durability upon laundering.

The silicone softener may be a polysiloxane, which is a polymercomprising Si—O moieties. Suitable silicone softener may be selectedfrom (a) non-functionalized siloxane polymers, (b) functionalizedsiloxane polymers, and combinations thereof. The functionalized siloxanepolymers may comprise an aminosilicone, silicone polyether, polydimethylsiloxane, cationic silicones, silicone polyurethane, silicone polyureas,or mixtures thereof. The silicone softener may comprise a cyclicpolysiloxane.

Suitable silicone softener may be linear, branched or cross-linked. Thesilicones may comprise silicone resins. Silicone resins are highlycross-linked polymeric siloxane systems. The cross-linking is introducedthrough the incorporation of trifunctional and tetrafunctional silaneswith monofunctional or difunctional, or both, silanes during manufactureof the silicone resin.

The non-functionalized siloxane polymer may comprise polyalkyl and/orphenyl silicone fluids, resins and/or gums.

Functionalized siloxane polymers may comprise one or more functionalmoieties selected from the group consisting of amino, amido, alkoxy,hydroxy, polyether, carboxy, hydride, mercapto, sulfate phosphate,and/or quaternary ammonium moieties. These moieties may be attacheddirectly to the siloxane backbone through a bivalent alkylene radical ormay be part of the backbone. Suitable functionalized siloxane polymersinclude materials selected from the group consisting of aminosilicones,amidosilicones, silicone polyethers, silicone-urethane polymers,quaternary ABn silicones, amino ABn silicones, and combinations thereof.

The functionalized siloxane polymer may comprise a silicone polyether.In general, silicone polyethers comprise a polydimethylsiloxane backbonewith one or more polyoxyalkylene chains. The polyoxyalkylene moietiesmay be incorporated in the polymer as pendent chains or as terminalblocks.

The functionalized siloxane polymer may comprise an aminosilicone, forexample, a monoamine, a diamine, or mixtures thereof. The functionalgroup may comprise a primary amine, a secondary amine, a tertiary amine,quaternized amines, or combinations thereof.

In a certain embodiment of the present invention the silicone softeneris an aminosilicone or an amino-functionalized siloxane, wherein theamino group is attached to the siloxane backbone through a bivalentalkylene radical.

Fabric softener are commercially available, for example, from HuntsmanCorporation under the tradename ULTRAPHIL® or ULTRATEX®.

The particles of the present invention are formed by contacting apayload with vinyltriethoxy silane monomer and at least one otherethylenically unsaturated monomer, so that the monomers assemble aroundthe payload. The monomers are then polymerized to yield a polymericshell matrix around the payload so that the polymeric shell matrixsurrounds the payload or binds directly to the payload.

In a certain embodiment of the present invention, the payload ischemically bonded to the shell matrix of the functionalized particle. Incase the payload is a functionalized silicone softener, the reactiveradical of the particle shell matrix may react with the functionalmoiety of the silicone softener, for example, an amino group, to form acovalent bond between the silicone softener and the shell matrix.

Alternatively, a functionalized particle can first be prepared withoutthe payload being present by polymerizing vinyltriethoxy silane and atleast one other ethylenically unsaturated monomer to form the polymericshell matrix, after which the particle thus formed is exposed to apayload under suitable conditions so that the payload is absorbed intoand entrapped in the polymeric matrix.

Appropriately, the preparation of the functionalized particles of thepresent invention is accomplished by polymerization of the monomers inan oil-in-water dispersion. The payload is finally taken up into theinteriors of the particles by including it in the hydrophobic oil-phasein advance. As required, the particles of this invention may containplasticizers, paraffins, animal and vegetable oils, silicone oils andsynthetic resins (e.g. xylene resins and ketone resins) so long as theyare inert to the monomers.

In a typical embodiment of the preparation of the functionalizedparticles of the present invention, the payload along with an emulsifieris dispersed in water. If the payload is a solid or a highly viscousliquid, it is appropriately first dissolved in a suitable hydrophobicorganic solvent that is immiscible in water. Upon applying high shearforces an emulsion of finely dispersed oil droplets in water is obtainedcomprising the payload. Afterwards the initiator is added to theoil-in-water emulsion at room temperature. Then, the monomers thatinclude the functionalized monomers carrying reactive radicals are addedto polymerize at an elevated temperature and form a polymer shell aroundthe payload. The resulting particles contain the payload that isembedded or entrapped and carry reactive functional groups on itspolymer surface capable of binding to a substrate to be treated, such asfibers of a textile or web.

The hydrophobic oil-phase containing to be dispersed in the aqueousphase may be reduced in viscosity by adding, as required, a non-reactivehydrophobic organic solvent. The amount of the organic solvent in thiscase is suitably not more than 80% by weight based on the weight of theentire hydrophobic phase. Examples of organic solvents that can be usedinclude aromatic hydrocarbons; aliphatic hydrocarbons; esters, such asdimethylphtalate; ethers; and ketones. As required, these organicsolvents may be removed by heating or pressure reduction during or afterforming the polymer microparticles.

The aqueous phase in which the hydrophobic phase is to be dispersed maycontain 0.1 to 20% by weight based on the aqueous phase of at least oneprotective colloid such as polyvinyl alcohol, hydroxyalkyl celluloses,carboxyalkyl celluloses, gum arabic, polyacrylates, polyacrylamides,polyvinylpyrrolidone and ethylene maleic anhydride copolymer. Theaqueous phase may contain 0.1 to 10% by weight based on the aqueousphase of nonionic, anionic or cationic surface-active agents, such as,for example, Polysorbate 80.

The step of dispersing the hydrophobic phase in the aqueous phase iscarried out at a temperature of from e.g. 5 to 90° C. to stabilize thedispersion. The dispersion may be carried out easily by a suitabledispersing device such as a high speed agitator, homogenizer, ahomodisperser or a propellar-type general stirrer or by a customaryaction.

In many cases, it is preferred to stir the dispersion mildly by using apropellar-type stirrer after the end of the dispersing step.

The average particle size is dependent on the temperature and theagitation speed, whereby a high agitation speed and a high temperaturefavor a small particle size. Furthermore, average particle size can becontrolled by the viscosity of the reaction medium. The viscosity may beadjusted by adding viscosity regulating agents or thickeners such ascommercially available alginate thickeners, starch ethers or locust beanflour ethers, sodium alginate on its own or in admixture with modifiedcellulose, e.g. methylcellulose, ethylcellulose, carboxymethylcellulose,hydroxyethylcellulose, methylhydroxyethylcellulose, hydroxypropylcellulose or hydroxypropyl methylcellulose, especially with preferablyfrom 20 to 25% by weight carboxymethylcellulose. Synthetic thickenersthat may be mentioned are, for example, those based on poly(meth)acrylicacids, poly(meth)acrylamides or polyvinyl pyrrolidones.

Dependent on their particle size the functionalized particles of thepresent invention are also referred to as micro-particles ornano-particles.

Polymerization can be accomplished by procedures known in the art and iscommonly accomplished by heat or by radiation, such as UV light or gammarays. Catalysts or photo- or thermal-initiators are suitably used toprepare the functionalized particles of the present invention. Suchinitiators and catalysts are well known in the art and are commerciallyavailable. There are mentioned, in particular, radical polymerizationinitiators commercially available from Wako Pure Chemical Industries,such as 2,2′-azobis[2-(2-imidazolin-2 yl)propane]dihydrochloride (VA044) or AIBN.

The polymerization initiator is used in an amount, for example, of from0.05 to 1.0 wt %, preferably 0.1 to 0.5 wt % based on the total weightof the emulsion applied for preparation of the functionalized particles.

In case the payload is a functionalized silicone softener, the weightratio of monomer to silicone softener is, for example, of from 1:10 to10:1, preferably 1:4 to 4:1 and especially 2:1 to 1:2.

The resulting particles are used according to the respective purposes.They may be used in the form of a fine powder after drying them by aspray drying method, a concentric separating drying method, a filtrationdrying method or a fluidized bed drying method. Likewise, functionalizedparticles may be used as a dispersion in water.

In the functionalized particles of the invention so obtained, thereaction is sufficiently completed to such an extent that no appreciabletrace of the unreacted monomer is seen in the interior. Accordingly, theparticles are very tough and have excellent solvent resistance.

Accordingly, the present invention also relates to a process for thepreparation of the functionalized particles according to the presentinvention, which process comprises the steps of preparing anoil-in-water dispersion and causing polymerisation of vinyltriethoxysilane and at least one other ethylenically unsaturated monomercopolymerizable with vinyltriethoxy silane at the oil-water interface inthe presence of the payload, wherein the variables are as defined andpreferred above.

The functionalized particles according to the present invention reactwith various compounds or substrates which contain nucleophilic groups,e.g. —OH, —NH or —SH, with their reactive radicals attached to theirouter shell. The reactive radicals form covalent bonds at roomtemperature or elevated temperatures of from, for example, 0 to 230° C.,preferably 20 to 80° C. in wet applications and 120 to 180° C. in dryapplications, which may be accomplished in the presence of e.g. alkali,such as soda, sodium hydroxide or potassium hydroxide, as it is known inthe art of textile dyeing or printing with reactive dyestuffs.

Accordingly, the present invention relates also to a process for thepreparation of a substrate modified with the functionalized particles,comprising treating the said substrate with the functionalized particlesaccording to the present invention or the functionalized particlesprepared in accordance with the present invention, so that thefunctionalized particles chemically bind to the substrate, wherein thevariables are as defined and preferred above.

Preferred as the substrates are fiber materials containing hydroxylgroups or containing nitrogen, such as textile fiber materials,keratineous fibers, e.g. human hair, or paper, preferably textile fibermaterials. Textile fiber materials can be in the form of fiber, yarn orpiece goods, such as non-wovens, knitted and woven goods, pile fabricsor terry goods. Examples are silk, wool, polyamide fibers andpolyurethanes, and preferably all types of cellulosic fiber materials.Such cellulose fiber materials are, for example, the natural cellulosicfibers, such as cotton, linen and hemp, as well as cellulose andregenerated cellulose. The functionalized microparticles according tothe invention are also suitable for finishing fibers containing hydroxylgroups which are contained in blend fabrics, for example mixtures ofcotton with polyester fibers or polyamide fibers. The functionalizedparticles according to the invention are particularly suitable forfinishing cellulose containing textile fiber materials, such as cottoncontaining textile fiber materials. They can furthermore be used forfinishing natural or synthetic polyamide fiber materials.

The functionalized microparticles according to the present invention areapplied to the textile goods in aqueous solution, in analogy to thedyeing processes known for reactive dyes or finishing processes intextile industry. They are suitable for spray-, exhaust- and for thepad-method, in which the goods are impregnated with aqueous solutions,which may contain salts. Dyeing machines customary in dyeing withreactive dyes are preferably utilized for this. The functionalizedmicroparticles according to the present invention are fixed, ifappropriate after an alkali treatment under the action of heat, steam orby storage at room temperature for several hours, thereby forming achemical bond with the substrate. The functionalized particles accordingto the present invention can also be applied in the presence ofcrosslinking agents or resin finish, for example, dimethylol-urea,dimethoxy-methyl-urea, trimethoxy-methyl-melamin,tetramethoxy-methyl-melamine, hexamethoxy-methyl-melamine,dimethylol-dihydroxy-ethylene-urea, dimethylol-propylene-urea,dimethylol-4-methoxy-5,5′-dimethyl-propylene-urea,dimethylol-5-hydroxypropylene-urea, butane-tetra-carboxylic-acid, citricacid, maleic acid, bonding agents, for example, acrylates, silicones,urethanes, butadienes, in a textile finishing process which may resultin superior effect durability. Such textile finishing processes aredescribed, for example, in DE-A-40 35 378. After the fixing, thefinished substrates are rinsed thoroughly with cold and hot water, ifappropriate with the addition of an agent which has a dispersing actionand promotes diffusion of the non-fixed portions.

The finished substrates contain, for example, 0.1 to 25% by weight,preferably 1 to 10% by weight, of the functionalized microparticlesaccording to the present invention, based on the total weight of thesubstrate.

The textile fabrics finished with the silicone softener containingfunctionalized particles of the present invention are distinguished bytheir durable softness and excellent water retention. Therefore, thesilicone softener containing functionalized particles of the presentinvention are in particular suitable for the durable finishing of terrytowels to impart softness and excellent handle even after multiplelaundries and maintaining at the same time a high degree of waterretention.

The following Examples illustrate the present invention. Parts andpercentages are by weight unless otherwise specified.

PREPARATION EXAMPLE 1

64.3 g of a suitable silicone softener (containing 30.89 gm of activesilicone content), 0.64 g polysorbate 80 and 25 g of deionized water areadded to a 3 neck-glass reactor equipped with a condenser, a thermometeran agitator and a dropping funnel. The mixture is stirred at 350 rpm for10 to 15 minutes and nitrogen is purged through the mixture. Then 0.42 gof 2,2′-azobis[2-(2-imidazolin-2-yl) propane] dihydrochloride are addedto the mixture under stirring at room temperature. The temperature ofthe mixture is slowly raised to 35 to 40° C. within 10 to 15 minutes andmaintained at this temperature. Subsequently, 1.55 g of vinyltriethoxysilane, 1.55 g of glycidyl methacrylate and 5.79 g of styreneare added to the reaction mixture at 35 to 40° C. under stirring. Afterthe addition of the monomers is completed the temperature of thereaction mixture is increased to 50 to 55° C. and stirring is continuedfor 4 h under a nitrogen atmosphere. Afterwards the reaction mixture isallowed to cool to 25 to 35° C. The concentration of unreacted monomeris verified by GC and HPLC. The content of residual unreacted styrene isbelow 0.09%. Afterwards water is added to adjust the desired solidcontent of 35 to 38%. The dispersion of the functionalized particlesthus obtained shows a good shelf life even upon prolonged storage at 40°C.

APPLICATION EXAMPLE 1

A cotton fabric/towel is passed through padding mangle to wet thefabric/towel with water. Subsequently, the wet fabric/towel is passedthrough 1-liter application bath prepared using 50 g of encapsulatedsilicone softener obtained in accordance with Preparation Example 1 and10 g of UVITEX® BST LIQ. The pH of application bath is adjusted to 5.5using acetic acid. The pick-up of the cotton fabric/towel is 15±2%. Thetreated wet cotton fabric/towel is dried and cured at 120±5° C. for 10minutes. After drying and curing the fabric is tumble dried for 20minutes with hot air of a temperature of 45° C. The fabric/towel thustreated is kept for conditioning at 25±5° C. for 1 day.

The treated fabric/towels are tested for initial and 10 Home Laundering(HL). Washing is done as per European 7A Home Laundering method. Initialsoftness, softness upon washing and water retention of treated towel arerecorded after conditioning. Water retention in % is determinedaccording to ASTMD 4772. An untreated fabric/terry towel ideally has awater retention of about 70%.

The fabric/towel treated in accordance with Application Example 1 showsa good softness/handle even after 10 home laundries and an initial waterretention of 55±5%.

EXAMPLES 2 TO 6 (PREPARATION AND APPLICATION)

Following a procedure analogous to that described in Example 1, butusing the monomers given in Table 1 there are obtained thefunctionalized particles of Examples 2 to 6 with the properties given inTable 1.

TABLE 1 Monomer concentration [wt %] Shelf Glycidyl Monomer/ life WaterHandle Vinyltriethoxy meth- Vinyl silicone Initiator at retention afterEx Styrene silane acrylate pyrrolidone ratio [wt %]** 40° C. [%] 10 HL 29.3 4.68 4.68 1:2 0.9 yes 12 yes 3 5 2.5 1 1:2 0.5 yes 30 yes 4 5 2.5 11   1:2.3 0.5 yes 10 yes 5 7.5 2 2 1.6:1   0.5 yes 48 yes 6* 7.4 1.961.96 1.5:1   0.5 yes 46 yes *Example 6 contains in addition to the othermonomers 1 wt % of acrylic acid and 0.01 wt % of3-(trimethoxysilyl)propyl methacrylate. **[wt %] is based on the totalweight of the emulsion applied for preparation of the functionalizedparticles.

The fabric/towels treated in accordance with Examples 2 to 6 show a goodsoftness/handle even after 10 home laundries and a good water retention.

1. Functionalized particles comprising a shell and a core and a payloadthat is embedded or entrapped, wherein the shell comprises a matrixobtained by interfacial polymerisation of vinyltriethoxy silane and atleast one other ethylenically unsaturated monomer copolymerizable withvinyltriethoxy silane, said functionalized particles being capable tochemically bind to a substrate.
 2. Functionalized particles according toclaim 1, wherein the at least one other ethylenically unsaturatedmonomer is a hydrophobic monomer.
 3. Functionalized particles accordingto claim 2, wherein the at least one other ethylenically unsaturatedhydrophobic monomer is styrene or glycidyl methacrylate. 4.Functionalized particles according to claim 2, wherein the at least oneother ethylenically unsaturated hydrophobic monomer is styrene andglycidyl methacrylate.
 5. Functionalized particles according to claim 1,wherein the payload is a silicone softener.
 6. Functionalized particlesaccording to claim 1, wherein the payload is chemically bonded to thematrix of the functionalized particle.
 7. A process for the preparationof the functionalized particles according to claim 1, which processcomprises the steps of preparing an oil-in-water dispersion and causingpolymerisation of vinyltriethoxy silane and at least one otherethylenically unsaturated monomer copolymerizable with vinyltriethoxysilane at the oil-water interface in the presence of the payload.
 8. Aprocess for the preparation of a substrate modified with functionalizedparticles, comprising treating the substrate with the functionalizedparticles according to claim 1 to chemically bind the functionalizedparticles to the substrate.
 9. The process according to claim 8, whereinthe substrate is a fiber material containing hydroxyl groups orcontaining nitrogen.
 10. The process according to claim 9, wherein thefiber material is cellulose containing textile fiber material.
 11. Asubstrate modified with functionalized particles obtained according tothe process of claim 8.